Arenes amidation

McGregor, W. McKervey, M.A. Schwing-Weill, M.-J. Vetrogon. V. Wechsler, S. Extraction and solution thermodynamics of coinplexation of alkali and alkaline-earth cations by calix[4]arene amides. J. Chem. Soc., Perkin 21. Trans., 2 Phys. Org. Chem. 1995, 3. 453-461. 

The preparation of amines by the methods described m this section involves the prior synthesis and isolation of some reducible material that has a carbon-nitrogen bond an azide a nitrile a nitro substituted arene or an amide The following section describes a method that combines the two steps of carbon-nitrogen bond formation and reduction into a single operation Like the reduction of amides it offers the possibility of prepar mg primary secondary or tertiary amines by proper choice of starting materials... 

In some instances the attack of the arene on the nitrilium salt occurs at the ipso carbon rather than the ortho carbon. For example, the Bischler-Napieralski cyclization of phenethyl amide 10 affords a 2 1 mixture of regioisomeric products 11 and 12. The formation of 12 presumably results from attack of the ipso aromatic carbon on the nitrilium salt 13 followed by rearrangement of the spirocyclic carbocation 14 to afford 15, which upon loss of a proton vields product 12. ... 

Kimura and coworkers [17], Diamond [18], and Damien et al. [19] have described that the polymeric calix-[4]arenes have been used as ionophores in ion selective electrodes for Na (based on calixarene esters and amides) and for Na and Cs (based on p-alkylcalixarene acetates). The electrodes are stated to function as poten-tiometric sensors as well, having good selectivity for primary ion, virtually no response to divalent cations, and being stable over a wide pH range. 

Other recent works in this field, studies on the transport of alkali and alkaline earth cations with p-zerr-butyl calix[n]arene esters and amides, were carried out by Arnaud-Neu et al. [20] and Casnati et al. [21]. They prepared 1,3-alternate calix[4]arene-crown-6 as a new class of cesium selective ionophore. 

Our recent studies on effective bromination and oxidation using benzyltrimethylammonium tribromide (BTMA Br3), stable solid, are described. Those involve electrophilic bromination of aromatic compounds such as phenols, aromatic amines, aromatic ethers, acetanilides, arenes, and thiophene, a-bromination of arenes and acetophenones, and also bromo-addition to alkenes by the use of BTMA Br3. Furthermore, oxidation of alcohols, ethers, 1,4-benzenediols, hindered phenols, primary amines, hydrazo compounds, sulfides, and thiols, haloform reaction of methylketones, N-bromination of amides, Hofmann degradation of amides, and preparation of acylureas and carbamates by the use of BTMA Br3 are also presented. 

Fagnou and co-workers reported on the use of a palladium source in the presence of different phosphine ligands for the intramolecular direct arylation reaction of arenes with bromides [56]. Later, they discovered that new conditions employing palladium complex 27 promoted the direct arylation of a broad range of aryl chlorides to form six- and five-membered ring biaryls including different functionalities as ether, amine, amide and alkyl (Scheme 7.11) [57]. 

Ohto, K. Yamaga, H. Murakami, E. Inoue, K. Specific extraction behavior of amide derivative of calix-4-arene for silver (I) and gold (III) ions from highly acidic chloride media. Talanta 1997, 44, 1123-1130. 

U. Schadel, F. Sansone, A. Casnati, and R. Ungaro, Synthesis of upper rim calix [4] arene divalent glycoclusters via amide bond conjugation, Tetrahedron, 61 (2005) 1149-1154. 

Hydrolysis of epoxides and arene oxides Hydrolysis of amides and esters Hydrolysis of glycosides... 

Klumpp, D. A. Rendy, R. Zhang, Y. Gomez, A. McElrea, A. Dicationic Intermediates Involving Protonated Amides Dual Modes of Reactivity Including the Acylation of Arenes. Org. Lett. 2004, 6,1789-1792. 

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